This is a spin on the average 'Medieval Challenge' in which you have to play as the royal family - in this challenge, you must play as a peasant 'heir' and try and work your way up in life as much as you can.
There are three ways to do this.
1: Become a lover of a member of royalty - be it the king, a prince, a cousin, or what have you. You may bear him children, but you may not marry him unless you are a high enough status.
2: Marry into a higher class - however, there are certain classes you can only marry if you have already reached a higher class.
3: Work for it! If you make enough money, you can move up classes and therefore have more opportunities.

CLASSES (colour-coded - you should adhere to this so you can tell the difference between each class) AND THE RULES OF EACH CLASS:

Your playable Sim must start out as a child within a large family. (I would recommend making them a teen.)

LOWER CLASS

PEASANT: To begin with, your main Sim must be a member of a large family within the Peasant class. Use familyfunds to drop their funds down to 250 simoleans after you've built their house. Peasants wear brown and cannot wear any 'fancy-looking' clothes, as they are only for the higher classes. Their outfits must only be simple and fit in with what peasants would wear at the time. Peasant sims cannot wear any obvious makeup - they can wear blush, as women would often pinch their cheeks to give themselves a little blush on the cheeks, and they can wear a subtle lipstick. They can also have eyelashes in the form of makeup, but nothing more than that. A nice touch would be to download a 'cheekbone' blush overlay, and use it to show that they do not have enough food. They can only have the 'fit' body type or the default body type, as they would not have enough money to feed themselves to the point of becoming overweight. For getting new food, they may pick fruit or fish. Peasants may work in these careers:
⦁ Criminal
⦁ Slacker
⦁ Adventurer
⦁ Education
⦁ OR any custom careers that you deem suitable for members of the lower class.
However, they can only reach level 4 of these careers. If your Sim gets a promotion to level 5, they must quit their job and try for a new one.
Peasant sims can marry: Merchants and other peasants. They can also, should they come into contact with an aristocrat or member of royalty, attempt to woo them and become a mistress. Be careful! If the member of royalty or aristocrat rebuffs their advances, you must lower everyone's relationship with the playable Sim using boolprop or another mod, as this would lower their reputation and shun them.
If a Peasant Sim earns 10,000 simoleans, they move up into the Merchant class.
They must live in small, cheaply furnished huts and cannot have any services (maid, gardener, etc...)

MERCHANT: Congratulations! Your Sim is climbing their way up, and is now a Merchant! Merchants wear grey and also cannot wear any fancy-looking clothes. Their outfits must be simple, but the clothes can be a little showier than those of the peasants, with jewellery. Merchant sims cannot wear any obvious makeup either, but they can at least wear a little bit of colour on their lips, nothing TOO bright or noticeable. I would also recommend that these sims have a slimmer body type, but the head of the household can grow overweight as they do have plenty of money for food. For food, they may order groceries, pick fruit, or fish. Merchants may either start a home business, or work in these careers:
⦁ Business
⦁ Criminal
⦁ Culinary
⦁ Medicine
⦁ Slacker
⦁ Show Business
⦁ OR any custom careers that you deem suitable for merchants.
However, they can only reach level 6 of these careers. If your Sim gets a promotion to level 7, they must quit their job.
Merchant sims can marry, peasants, lower middle class, and other merchants. They can also attempt to woo the higher classes and become a mistress. Their reputation still drops if their attempts are rebuffed, but not quite as badly as it would if they were a peasant.
If a merchant Sim earns 15,000 simoleans, they move up into the lower middle class.
They must live in 'townhouses' and can have a maid.

MIDDLE CLASS

LOWER MIDDLE CLASS: You're moving up, that's for sure! Lower-middle class members wear green and their outfits are much fancier than the previous two classes, although not quite truly fancy yet. Lower mid class sims can wear the same makeup as the previous classes, but they may wear a light subtle eyeshadow if they wish, as well. They can have any kind of body type. For food, they may order groceries. They cannot fish or pick fruit as that would be unbecoming of folks of their status. Lower middle class may work in these careers:
⦁ Education
⦁ Business
⦁ Culinary
⦁ Medicine
⦁ Slacker
⦁ Military (the equivalent of a knighthood)
⦁ OR any custom careers that you deem suitable for members of the middle class.
They can reach any level of this career track.
Lower middle class sims can marry: Merchants, middle class (higher), or other lower middle class. They can also attempt to woo the higher classes and become a mistress. Their reputation barely drops if their attempts are rebuffed, but it is still a drop.
If a lower middle class Sim earns 20,000 simoleans, they move up into the middle class.
They must live in large houses and can have a maid and nanny.

MIDDLE CLASS: You're on fire! Middle class members wear red and their outfits are slightly more sophisticated than the previous class, although not quite there yet. Middle class sims can wear the same makeup as the previous classes as well as a darker lipstick. They can have any kind of body type. For food, they may order groceries. Lower middle class may work in these careers:
⦁ Slacker
⦁ Education
⦁ Business
⦁ Culinary
⦁ Medicine
⦁ Military
⦁ OR any custom careers that you deem suitable for members of the middle class.
They can reach any level of this career track.
Middle-class sims can marry: Lower middle class, aristocrats or other middle-class members. They can also attempt to woo the higher classes and become a mistress. Their reputation does not drop if their advances are rebuffed, though you lose points.
If a middle-class Sim earns 30,000 simoleans, they move up into the aristocracy.
They must live in larger houses and can have any services that they want.

HIGHER CLASS

ARISTOCRACY: Look at where you are, look at where you started! Aristocrat members wear blue and their outfits are unbelievably fancy, but not as fancy as the royalty. Aristocrats may wear whatever makeup they wish. They can have any kind of body type. For food, they may order groceries. Aristocrats may work in these careers:
⦁ Business
⦁ Politics (the equivalent of being seated on the king's council)
⦁ Law Enforcement
⦁ Politics
⦁ Slacker
⦁ Military
⦁ OR any custom careers that you deem suitable for members of the higher class.
They can reach any level of this career track.
Aristocrat sims can marry: Middle class, royalty or other aristocrats. They can become mistresses, and their reputation does not drop if rebuffed, though you lose points.
Aristocrats cannot move up into the royalty via earning money, but they can be entered into arranged marriages with royals.
They must live in mansions and must have services like maids and nannies.

ROYALTY: Started from the bottom, now we're here! Royalty wears purple and their outfits are as fancy and outrageous as possible. Royalty can wear whatever makeup they wish. They can have any kind of body type. For food, they may order groceries. Royalty may work in these careers:
⦁ Slacker
⦁ Politics
⦁ Military
⦁ OR any custom careers that you deem suitable for members of the royalty. If there is a King/Queen custom career, that would be good.
They can reach any level of this career track.
Royalty can marry aristocrats. I wouldn't advise marrying them to other members of royalty unless you have a neighbouring kingdom (add a sub-hood) with its own royalty. Male members of royalty cannot marry anyone who has children unless it is their mistress. If their spouse was married before, it is fine, as it is entirely possible that the spouse had an unconsummated marriage. Of course, that may not have been the case, but with no children, how could the royalty know?
The royalty sims should have unlimited funds.
They must live in castles and must have every service (maid, nanny, gardener, etc...).
If you reach this level, you can only now bring your family from the beginning, and they will go from peasants to the aristocracy.

EXTRA CLASSES - DO NOT JOIN

NUNS AND PRIESTS: These NPCs wear black, and dress as appropriate for their jobs. They preside in nunneries and houses near the church, and the priest owns the church. If you wish, you can send your daughters or sisters to become a nun, meaning they leave home and move out, and you will gain a sum of 1000 simoleans for each daughter/sister. Use 'kaching' to gain this.WITCHES AND WARLOCKS: These NPCS wear the standard clothes that they usually do. You can associate with them, but you cannot ask to become a witch or warlock.

RULES AND RECOMMENDATIONS:

NOTE: If there is an asterisk after the rule, it is completely optional if you want to do a modern-day version of this challenge (which would be cool!)
⦁ You must move your Sim into a larger house every time they move up a class. Use the cheat 'familyfunds' or use the Mortgage Shrubs to make it cheap.
⦁ Unless your Sim is married or has children, they cannot bring anyone with them if they move up a class.
⦁ Every time a Sim woohoos, you must use 'try for baby' as there was no reliable birth control.*
⦁ I would recommend that unless your Sim becomes a mistress, they do not woohoo out of wedlock as if they get pregnant or get another Sim pregnant, they would lose reputation.
⦁ Other than previously specified, do not use any money cheats.
⦁ I would use a mod that allows adults and teens to be in a relationship and marry, as that was common back then. If you feel uncomfortable with this, that is completely fine and this is absolutely optional.*
⦁ Don't use phones, TVs, computers, or anything of the sort. If there are medieval alternatives (i.e, I saw a phone alternative that was a magical scroll), then feel free to use that!*
⦁ Only male sims can propose, as the female could not pass on her name.*
⦁ If your playable Sim is a female, to get their lover to propose to them, they must ask their lover to move in. Then, the lover can propose and they can (if moving up a class) move out and into the lover's home.*
⦁ NPC's may only marry Sims from the merchant class or lower.
⦁ Hacks and mods are only allowed to make the neighbourhood more historically accurate and realistic.*
⦁ If your Sim dies before they reach your personal goal, you can carry on their legacy with their offspring or a sibling from the beginning of the game.
⦁ I recommend using time-passing mods and longer lifespan mods.
⦁ Other than for the reputation drops, you are not allowed to change the relationships with other sims via cheats.
⦁ Maxmotives is only allowed once you hit the aristocracy class.
⦁ You cannot move down a class unless your reputation is below halfway and you have less money than the requirement for your class.